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Synfacts 2015; 11(10): 1105
DOI: 10.1055/s-0035-1560273
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Carbonyl Reduction with a Supported Ketoreductase

Contributor(s):
Yasuhiro Uozumi
,
Kotaro Yamamura
Li H, * Moncecchi J, Truppo MD. Merck & Co., Rahway, USA
Development of an Immobilized Ketoreductase for Enzymatic (R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethanol Production.

Org. Process Res. Dev. 2015;
19: 695-700
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Further Information

Publication History

Publication Date:
18 September 2015 (online)

 
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Key words

enzymes - biocatalysis - hydrogenation - ketones

Significance

Immobilized ketoreductase P1B2 (immob P1B2), prepared as shown in eq. 1, catalyzed the asymmetric transfer-hydrogenation of ketones in 90:10 propan-2-ol–water to give the corresponding alcohols in up to 100% conversion and up to >99% ee (eq. 2). This reaction was used in a 50 g scale reduction of 3,5-[bis(trifluoromethyl)phenyl]ethanone (1) (eq. 3).


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Comment

Immob P1B2 was recovered and reused nine times without any loss of its catalytic performance. The catalyst was also used in a flow transfer hydrogenation of ketone 1.


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